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Camps quinoline synthesis



The Camps quinoline synthesis (also known as the Camps cyclization) is a chemical reaction whereby an o-acylaminoacetophenone is transformed into two different hydroxyquinolines (products A and B) using hydroxide ion.[1][2][3][4]

Additional recommended knowledge

The relative proportions of the hydroxyquinolines (A and B) produced are dependent upon the reaction conditions and structure of the starting material. Although the reaction product is commonly depicted as a quinoline (the enol form), it is believed that the keto form predominates in both the solid state and in solution, making the compound a quinolone [5].

An example of the Camps reaction is given below [5]:

References

  1. ^ Camps, R.; Ber. 1899, 22, 3228.
  2. ^ Camps, R.; Arch. Pharm. 1899, 237, 659.
  3. ^ Camps, R.; Arch. Pharm. 1901, 239, 591.
  4. ^ Manske, R. H. F.; Chem. Rev. 1942, 30, 127. (Review)
  5. ^ a b Sequential Cu-Catalyzed Amidation-Base-Mediated Camps Cyclization: A Two-Step Synthesis of 2-Aryl-4-quinolones from o-Halophenones Jones, C. P.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem.; (Article); 2007; 72(21); 7968-7973. doi:10.1021/jo701384n

See also

  • Conrad-Limpach synthesis
  • Doebner reaction
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Camps_quinoline_synthesis". A list of authors is available in Wikipedia.
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